There are few transitions in life more profound than moving from “we” to “me.” Whether through the passing of a spouse or a divorce, the change is emotional, financial, and deeply personal. For those approaching or already in retirement, this transition can be especially difficult.

He was known as the “Great Bear of Wall Street,” Jesse Livermore was one of the best known investors of the early 1900s. But his story is not a happy one. It raises the uncomfortable question: How can someone be so right … and still not succeed?

Where do those tax problems actually show up, and why do so many thoughtful investors ultimately pay more than necessary? In most cases, it’s not a lack of knowledge that drives this problem, but timing. The biggest tax mistake investors make isn’t misunderstanding the rules; it’s waiting too long to act.

There is a curious trait built into human nature: When something is painful, frightening or deeply disorienting, we don’t just want it to end — we want to forget it ever happened. COVID fits that description perfectly.

Most people reading this column — whether early in their careers or well into retirement — have had their entire financial lives shaped by the events between 1975 and 2025. And yet almost none of us were taught to study that period carefully. Instead, we’ve been conditioned by markets, media and our own wiring to obsess over what’s happening today and what might come next. Such a short-term obsession is the enemy of good investor behavior.